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A Concise Diastereoselective Total Synthesis of α-Ambrinol
(−)-cis-α-Ambrinol is a natural product present in ambergris, a substance of marine origin that has been highly valued by perfumers. In this paper, we present a new approach to its total synthesis. The starting material is commercially available α-ionone and the key step is an intramolecular Barbier...
| Autores principales: | , , , , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
MDPI
2023
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| Materias: | |
| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10145093/ https://www.ncbi.nlm.nih.gov/pubmed/37103369 http://dx.doi.org/10.3390/md21040230 |
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| author | López-Martínez, Josefa L. Torres-García, Irene Moreno-Gutiérrez, Irene Oña-Burgos, Pascual Rosales Martínez, Antonio Muñoz-Dorado, Manuel Álvarez-Corral, Míriam Rodríguez-García, Ignacio |
| author_facet | López-Martínez, Josefa L. Torres-García, Irene Moreno-Gutiérrez, Irene Oña-Burgos, Pascual Rosales Martínez, Antonio Muñoz-Dorado, Manuel Álvarez-Corral, Míriam Rodríguez-García, Ignacio |
| author_sort | López-Martínez, Josefa L. |
| collection | PubMed |
| description | (−)-cis-α-Ambrinol is a natural product present in ambergris, a substance of marine origin that has been highly valued by perfumers. In this paper, we present a new approach to its total synthesis. The starting material is commercially available α-ionone and the key step is an intramolecular Barbier-type cyclization induced by CpTiCl(2), an organometallic compound prepared in situ by a CpTiCl(3) reduction with Mn. |
| format | Online Article Text |
| id | pubmed-10145093 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2023 |
| publisher | MDPI |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-101450932023-04-29 A Concise Diastereoselective Total Synthesis of α-Ambrinol López-Martínez, Josefa L. Torres-García, Irene Moreno-Gutiérrez, Irene Oña-Burgos, Pascual Rosales Martínez, Antonio Muñoz-Dorado, Manuel Álvarez-Corral, Míriam Rodríguez-García, Ignacio Mar Drugs Article (−)-cis-α-Ambrinol is a natural product present in ambergris, a substance of marine origin that has been highly valued by perfumers. In this paper, we present a new approach to its total synthesis. The starting material is commercially available α-ionone and the key step is an intramolecular Barbier-type cyclization induced by CpTiCl(2), an organometallic compound prepared in situ by a CpTiCl(3) reduction with Mn. MDPI 2023-04-01 /pmc/articles/PMC10145093/ /pubmed/37103369 http://dx.doi.org/10.3390/md21040230 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
| spellingShingle | Article López-Martínez, Josefa L. Torres-García, Irene Moreno-Gutiérrez, Irene Oña-Burgos, Pascual Rosales Martínez, Antonio Muñoz-Dorado, Manuel Álvarez-Corral, Míriam Rodríguez-García, Ignacio A Concise Diastereoselective Total Synthesis of α-Ambrinol |
| title | A Concise Diastereoselective Total Synthesis of α-Ambrinol |
| title_full | A Concise Diastereoselective Total Synthesis of α-Ambrinol |
| title_fullStr | A Concise Diastereoselective Total Synthesis of α-Ambrinol |
| title_full_unstemmed | A Concise Diastereoselective Total Synthesis of α-Ambrinol |
| title_short | A Concise Diastereoselective Total Synthesis of α-Ambrinol |
| title_sort | concise diastereoselective total synthesis of α-ambrinol |
| topic | Article |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10145093/ https://www.ncbi.nlm.nih.gov/pubmed/37103369 http://dx.doi.org/10.3390/md21040230 |
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